Issue contents
Download PDF of article
Download CIF
3D view
Navigation
Highlighting
Dictionary of Crystallography reference
IUPAC Gold Book reference
more ...
Download citation
FormatBIBTeX
EndNote
RefMan
Refer
Medline
CIF
SGML
Plain Text
share
Previous article
Next article
Previous article
Issue contents
Download PDF of article
Download CIF
3D view
Navigation
Highlighting
Dictionary of Crystallography reference
IUPAC Gold Book reference
more ...
Download citation
FormatBIBTeX
EndNote
RefMan
Refer
Medline
CIF
SGML
Plain Text
share
Next article

organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 71| Part 8| August 2015| Pages o574-o575
https://doi.org/10.1107/S2056989015013286

Crystal structure of 2,3-dimeth­­oxy-5,6,7,8,13,13a-hexa­hydro-6a,8-di­aza­indeno­[2,1-b]phenanthrene methanol monosolvate

Shahobiddin M. Adizov,a* Abdusalom Sh. Saidov,a Kambarali K. Turgunov,a Rasul Ya. Okmanova and Bakhodir Tashkhodjaeva

aS.Yunusov Institute of the Chemistry of Plant Substances, Academy of Sciences of Uzbekistan, Mirzo Ulugbek Str. 77, Tashkent 100170, Uzbekistan
*Correspondence e-mail: adizovshahobiddin@yahoo.com

Edited by M. Weil, Vienna University of Technology, Austria (Received 8 July 2015; accepted 10 July 2015; online 15 July 2015)

The asymmetric unit of the title solvate, C21H22N2O2·CH3OH, contains one methanol solvent mol­ecule and one mol­ecule of the heterocycle that is built up by the fusion of four six-membered rings A, C, D, E and one five-membered ring B. The indole moiety (rings A and B) is essentially planar, with an r.m.s. deviation of 0.013 Å, whereas rings C and D adopt a twisted conformation with a trans-ring junction. In the crystal, two heterocyclic mol­ecules are associated with two methanol mol­ecules through mutual N—H⋯O and O—H⋯N hydrogen bonds, forming a centrosymmetric dimer.

CCDC reference: 1412105

Similar articles

1. Related literature

Synthetic details regarding the title compound were described by Saidov et al. (2014[Saidov, A. Sh., Alimova, M. & Vinogradova, V. I. (2014). IJCPS, 3, 9-12.]). For synthetic procedures of related compounds and their structures, see: Saidov et al. (2013[Saidov, A. Sh., Alimova, M., Levkovich, M. G. & Vinogradova, V. I. (2013). Chem. Nat. Compd. 49, 302-304.]). For another related crystal structure, see: Yu et al. (1995[Yu, H.-T., Vela, M. A., Fronczek, F. R., McLaughlin, M. L. & Barkley, M. D. (1995). J. Am. Chem. Soc. 117, 348-357.]).

[Scheme 1]

2. Experimental

2.1. Crystal data

  • C21H22N2O2·CH4O

  • Mr = 366.45

  • Triclinic, [P \overline 1]

  • a = 7.6080 (3) Å

  • b = 11.8061 (5) Å

  • c = 12.3327 (5) Å

  • α = 65.242 (4)°

  • β = 73.956 (4)°

  • γ = 75.724 (4)°

  • V = 955.81 (7) Å3

  • Z = 2

  • Cu Kα radiation

  • μ = 0.68 mm−1

  • T = 293 K

  • 0.42 × 0.25 × 0.12 mm

2.2. Data collection

  • Oxford Diffraction Xcalibur Ruby diffractometer

  • Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009[Oxford Diffraction (2009). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]) Tmin = 0.843, Tmax = 1.000

  • 19864 measured reflections

  • 3936 independent reflections

  • 2889 reflections with I > 2σ(I)

  • Rint = 0.046

2.3. Refinement

  • R[F2 > 2σ(F2)] = 0.040

  • wR(F2) = 0.120

  • S = 1.04

  • 3936 reflections

  • 256 parameters

  • H atoms treated by a mixture of independent and constrained refinement

  • Δρmax = 0.17 e Å−3

  • Δρmin = −0.17 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
N1—H1A⋯O3 0.907 (19) 1.982 (19) 2.880 (2) 170.1 (16)
O3—H3⋯N4i 0.91 (2) 1.95 (2) 2.840 (2) 165 (2)
Symmetry code: (i) -x, -y+1, -z+1.

Data collection: CrysAlis PRO (Oxford Diffraction, 2009[Oxford Diffraction (2009). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: XP in SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: publCIF (Westrip, 2010[Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.]).

Supporting information

CCDC reference: 1412105

Crystal structure: contains datablocks I, New_Global_Publ_Block. DOI: https://doi.org/10.1107/S2056989015013286/wm5184sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989015013286/wm5184Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2056989015013286/wm5184Isup3.cml

checkCIF report


Synthesis and crystallization top

The synthesis of the title compound was described previously (Saidov et al., 2014). Orange crystals were obtained in a methanol:chloro­form 1:1 (v/v) mixture by slow evaporation of the solvent at room temperature.

Refinement top

Carbon-bound H atoms were placed geometrically and treated as riding on their parent atoms, with C—H = 0.93 Å (aromatic), 0.97 Å (methylen) or 0.96 Å (methyl) and were refined with Uiso(H) = 1.2Ueq(C) for aromatic and methyl­ene hydrogens and Uiso(H) = 1.5Ueq(C) for methyl H atoms. The N- and O-bound H atoms were located in a difference Fourier map and were refined freely.

Related literature top

Synthetic details regarding the title compound were described by Saidov et al. (2014). For synthetic procedures of related compounds and their structures, see: Saidov et al. (2013). For another related crystal structure, see: Yu et al. (1995).

Structure description top

Synthetic details regarding the title compound were described by Saidov et al. (2014). For synthetic procedures of related compounds and their structures, see: Saidov et al. (2013). For another related crystal structure, see: Yu et al. (1995).

Synthesis and crystallization top

The synthesis of the title compound was described previously (Saidov et al., 2014). Orange crystals were obtained in a methanol:chloro­form 1:1 (v/v) mixture by slow evaporation of the solvent at room temperature.

Refinement details top

Carbon-bound H atoms were placed geometrically and treated as riding on their parent atoms, with C—H = 0.93 Å (aromatic), 0.97 Å (methylen) or 0.96 Å (methyl) and were refined with Uiso(H) = 1.2Ueq(C) for aromatic and methyl­ene hydrogens and Uiso(H) = 1.5Ueq(C) for methyl H atoms. The N- and O-bound H atoms were located in a difference Fourier map and were refined freely.

Computing details top

Data collection: CrysAlis PRO (Oxford Diffraction, 2009); cell refinement: CrysAlis PRO (Oxford Diffraction, 2009); data reduction: CrysAlis PRO (Oxford Diffraction, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: XP in SHELXTL (Sheldrick, 2008); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top
[Figure 1] Fig. 1. The molecular components of the title compound, with displacement ellipsoids drawn at the 50% probability level.
[Figure 2] Fig. 2. Hydrogen bonding between the molecular components, leading to the formation of dimers.
2,3-Dimethoxy-5,6,7,8,13,13a-hexahydro-6a,8-diazaindeno[2,1-b]phenanthrene methanol monosolvate top
Crystal data top
C21H22N2O2·CH4OZ = 2
Mr = 366.45F(000) = 392
Triclinic, P1Dx = 1.273 Mg m−3
Hall symbol: -P 1Melting point: 393(2) K
a = 7.6080 (3) ÅCu Kα radiation, λ = 1.54184 Å
b = 11.8061 (5) ÅCell parameters from 7310 reflections
c = 12.3327 (5) Åθ = 4.0–75.6°
α = 65.242 (4)°µ = 0.68 mm−1
β = 73.956 (4)°T = 293 K
γ = 75.724 (4)°Prism, orange
V = 955.81 (7) Å30.42 × 0.25 × 0.12 mm
Data collection top
Oxford Diffraction Xcalibur Ruby
diffractometer		3936 independent reflections
Radiation source: Enhance (Cu) X-ray Source2889 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.046
Detector resolution: 10.2576 pixels mm-1θmax = 75.8°, θmin = 4.0°
ω scansh = −9→8
Absorption correction: multi-scan
(CrysAlis PRO; Oxford Diffraction, 2009)		k = −14→14
Tmin = 0.843, Tmax = 1.000l = −15→15
19864 measured reflections
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.040H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.120 w = 1/[σ2(Fo2) + (0.069P)2 + 0.0547P]
where P = (Fo2 + 2Fc2)/3
S = 1.04(Δ/σ)max = 0.002
3936 reflectionsΔρmax = 0.17 e Å−3
256 parametersΔρmin = −0.17 e Å−3
0 restraintsExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0025 (6)
Crystal data top
C21H22N2O2·CH4Oγ = 75.724 (4)°
Mr = 366.45V = 955.81 (7) Å3
Triclinic, P1Z = 2
a = 7.6080 (3) ÅCu Kα radiation
b = 11.8061 (5) ŵ = 0.68 mm−1
c = 12.3327 (5) ÅT = 293 K
α = 65.242 (4)°0.42 × 0.25 × 0.12 mm
β = 73.956 (4)°
Data collection top
Oxford Diffraction Xcalibur Ruby
diffractometer		3936 independent reflections
Absorption correction: multi-scan
(CrysAlis PRO; Oxford Diffraction, 2009)		2889 reflections with I > 2σ(I)
Tmin = 0.843, Tmax = 1.000Rint = 0.046
19864 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0400 restraints
wR(F2) = 0.120H atoms treated by a mixture of independent and constrained refinement
S = 1.04Δρmax = 0.17 e Å−3
3936 reflectionsΔρmin = −0.17 e Å−3
256 parameters
Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.58933 (14)0.05796 (10)1.11979 (9)0.0544 (3)
O20.27998 (15)0.08093 (10)1.27098 (9)0.0582 (3)
O30.10908 (17)0.72865 (11)0.27339 (11)0.0653 (3)
N10.30388 (18)0.48439 (12)0.39691 (11)0.0499 (3)
N40.13746 (15)0.41753 (10)0.72574 (10)0.0430 (3)
C20.2862 (2)0.43976 (13)0.52151 (13)0.0457 (3)
C30.1738 (2)0.50958 (13)0.59986 (12)0.0462 (3)
H3A0.24040.57230.59510.055*
H3B0.05810.55230.57300.055*
C50.31440 (18)0.34322 (13)0.76212 (12)0.0437 (3)
H5A0.40350.40200.73380.052*
C60.3879 (2)0.25152 (14)0.69509 (13)0.0497 (3)
H6A0.51470.21470.70360.060*
H6B0.31390.18380.73050.060*
C70.37932 (19)0.32112 (14)0.56320 (13)0.0464 (3)
C80.45916 (19)0.28619 (14)0.45984 (13)0.0475 (3)
C90.5643 (2)0.17724 (16)0.44332 (16)0.0590 (4)
H9A0.59610.10630.50970.071*
C100.6200 (2)0.17645 (19)0.32772 (17)0.0669 (5)
H10A0.68950.10420.31630.080*
C110.5741 (2)0.28218 (19)0.22718 (16)0.0654 (5)
H11A0.61470.27920.14990.078*
C120.4700 (2)0.39083 (17)0.23980 (14)0.0578 (4)
H12A0.44050.46120.17240.069*
C130.4104 (2)0.39180 (15)0.35692 (13)0.0493 (3)
C140.0333 (2)0.48294 (13)0.80799 (13)0.0485 (3)
H14A−0.07280.53920.77600.058*
H14B0.11130.53290.81410.058*
C15−0.0305 (2)0.38641 (14)0.93244 (13)0.0502 (4)
H15A−0.09320.42860.98840.060*
H15B−0.11740.34180.92730.060*
C160.29541 (19)0.27694 (13)0.89861 (12)0.0438 (3)
C170.13271 (19)0.29376 (13)0.97944 (13)0.0455 (3)
C180.1258 (2)0.22773 (14)1.10490 (13)0.0493 (3)
H18A0.01620.23761.15900.059*
C190.2769 (2)0.14886 (13)1.14984 (13)0.0473 (3)
C200.44399 (19)0.13467 (13)1.06780 (13)0.0452 (3)
C210.45059 (19)0.19815 (13)0.94490 (13)0.0456 (3)
H21A0.56070.18870.89090.055*
C220.7633 (2)0.04838 (16)1.04086 (15)0.0574 (4)
H22A0.8558−0.00201.08830.086*
H22B0.79610.13110.99280.086*
H22C0.75550.00960.98810.086*
C230.1439 (3)0.12453 (19)1.35495 (15)0.0724 (5)
H23A0.17140.07931.43500.109*
H23B0.02460.11091.35490.109*
H23C0.14330.21301.33190.109*
C240.0459 (3)0.81552 (19)0.3320 (2)0.0782 (5)
H24A−0.05990.79000.39510.117*
H24B0.01220.89790.27370.117*
H24C0.14250.81780.36700.117*
H1A0.254 (2)0.5621 (17)0.3504 (15)0.060 (5)*
H30.014 (3)0.694 (2)0.2747 (18)0.085 (6)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0513 (6)0.0577 (6)0.0479 (6)0.0017 (5)−0.0120 (4)−0.0179 (5)
O20.0644 (7)0.0589 (6)0.0423 (6)−0.0024 (5)−0.0066 (5)−0.0166 (5)
O30.0602 (7)0.0617 (7)0.0753 (8)−0.0148 (6)−0.0117 (6)−0.0251 (6)
N10.0513 (7)0.0490 (7)0.0448 (7)−0.0092 (6)−0.0086 (5)−0.0129 (6)
N40.0425 (6)0.0410 (6)0.0441 (6)−0.0033 (5)−0.0078 (5)−0.0168 (5)
C20.0443 (8)0.0471 (7)0.0443 (7)−0.0111 (6)−0.0063 (6)−0.0151 (6)
C30.0470 (8)0.0412 (7)0.0476 (8)−0.0066 (6)−0.0094 (6)−0.0141 (6)
C50.0382 (7)0.0464 (7)0.0456 (7)−0.0057 (6)−0.0070 (6)−0.0176 (6)
C60.0483 (8)0.0512 (8)0.0455 (8)0.0031 (6)−0.0102 (6)−0.0195 (6)
C70.0430 (8)0.0499 (8)0.0452 (7)−0.0058 (6)−0.0068 (6)−0.0186 (6)
C80.0409 (8)0.0554 (8)0.0490 (8)−0.0098 (6)−0.0074 (6)−0.0217 (7)
C90.0531 (9)0.0632 (10)0.0638 (10)0.0000 (7)−0.0114 (7)−0.0318 (8)
C100.0594 (10)0.0801 (12)0.0719 (12)−0.0031 (9)−0.0079 (8)−0.0462 (10)
C110.0586 (10)0.0928 (13)0.0580 (10)−0.0202 (9)−0.0002 (8)−0.0432 (10)
C120.0548 (9)0.0743 (11)0.0481 (8)−0.0198 (8)−0.0061 (7)−0.0238 (8)
C130.0419 (8)0.0588 (9)0.0501 (8)−0.0149 (6)−0.0055 (6)−0.0215 (7)
C140.0467 (8)0.0461 (8)0.0540 (8)−0.0009 (6)−0.0090 (6)−0.0240 (7)
C150.0432 (8)0.0561 (8)0.0513 (8)−0.0028 (6)−0.0048 (6)−0.0256 (7)
C160.0422 (7)0.0452 (7)0.0456 (7)−0.0079 (6)−0.0063 (6)−0.0194 (6)
C170.0432 (8)0.0470 (7)0.0478 (8)−0.0071 (6)−0.0067 (6)−0.0206 (6)
C180.0466 (8)0.0526 (8)0.0470 (8)−0.0082 (6)−0.0010 (6)−0.0219 (7)
C190.0534 (9)0.0460 (7)0.0428 (7)−0.0087 (6)−0.0073 (6)−0.0178 (6)
C200.0466 (8)0.0438 (7)0.0481 (8)−0.0045 (6)−0.0115 (6)−0.0201 (6)
C210.0408 (7)0.0507 (8)0.0457 (8)−0.0056 (6)−0.0054 (6)−0.0212 (6)
C220.0457 (8)0.0602 (9)0.0602 (9)−0.0036 (7)−0.0108 (7)−0.0192 (8)
C230.0702 (12)0.0829 (12)0.0440 (9)0.0036 (9)−0.0024 (8)−0.0185 (9)
C240.0810 (13)0.0703 (12)0.0934 (14)−0.0119 (10)−0.0234 (11)−0.0362 (11)
Geometric parameters (Å, º) top
O1—C201.3658 (17)C10—H10A0.9300
O1—C221.4207 (18)C11—C121.376 (2)
O2—C191.3720 (17)C11—H11A0.9300
O2—C231.4143 (19)C12—C131.393 (2)
O3—C241.411 (2)C12—H12A0.9300
O3—H30.91 (2)C14—C151.512 (2)
N1—C131.3743 (19)C14—H14A0.9700
N1—C21.3782 (18)C14—H14B0.9700
N1—H1A0.907 (18)C15—C171.507 (2)
N4—C141.4706 (17)C15—H15A0.9700
N4—C31.4716 (17)C15—H15B0.9700
N4—C51.4849 (17)C16—C171.3885 (19)
C2—C71.355 (2)C16—C211.4040 (19)
C2—C31.4856 (19)C17—C181.403 (2)
C3—H3A0.9700C18—C191.373 (2)
C3—H3B0.9700C18—H18A0.9300
C5—C161.5115 (19)C19—C201.412 (2)
C5—C61.5374 (19)C20—C211.3735 (19)
C5—H5A0.9800C21—H21A0.9300
C6—C71.4959 (19)C22—H22A0.9600
C6—H6A0.9700C22—H22B0.9600
C6—H6B0.9700C22—H22C0.9600
C7—C81.433 (2)C23—H23A0.9600
C8—C91.399 (2)C23—H23B0.9600
C8—C131.418 (2)C23—H23C0.9600
C9—C101.374 (2)C24—H24A0.9600
C9—H9A0.9300C24—H24B0.9600
C10—C111.395 (3)C24—H24C0.9600
C20—O1—C22117.34 (11)C12—C13—C8121.50 (15)
C19—O2—C23116.67 (12)N4—C14—C15109.21 (11)
C24—O3—H3111.0 (13)N4—C14—H14A109.8
C13—N1—C2108.22 (13)C15—C14—H14A109.8
C13—N1—H1A126.7 (11)N4—C14—H14B109.8
C2—N1—H1A125.0 (11)C15—C14—H14B109.8
C14—N4—C3109.92 (10)H14A—C14—H14B108.3
C14—N4—C5111.77 (11)C17—C15—C14110.14 (12)
C3—N4—C5109.95 (10)C17—C15—H15A109.6
C7—C2—N1110.50 (13)C14—C15—H15A109.6
C7—C2—C3124.68 (13)C17—C15—H15B109.6
N1—C2—C3124.76 (13)C14—C15—H15B109.6
N4—C3—C2107.82 (11)H15A—C15—H15B108.1
N4—C3—H3A110.1C17—C16—C21119.03 (13)
C2—C3—H3A110.1C17—C16—C5122.61 (13)
N4—C3—H3B110.1C21—C16—C5118.33 (12)
C2—C3—H3B110.1C16—C17—C18119.08 (13)
H3A—C3—H3B108.5C16—C17—C15120.00 (13)
N4—C5—C16112.57 (11)C18—C17—C15120.86 (12)
N4—C5—C6108.21 (11)C19—C18—C17121.73 (13)
C16—C5—C6112.62 (11)C19—C18—H18A119.1
N4—C5—H5A107.7C17—C18—H18A119.1
C16—C5—H5A107.7O2—C19—C18124.92 (13)
C6—C5—H5A107.7O2—C19—C20115.89 (13)
C7—C6—C5109.45 (12)C18—C19—C20119.19 (13)
C7—C6—H6A109.8O1—C20—C21125.15 (13)
C5—C6—H6A109.8O1—C20—C19115.63 (12)
C7—C6—H6B109.8C21—C20—C19119.21 (13)
C5—C6—H6B109.8C20—C21—C16121.71 (13)
H6A—C6—H6B108.2C20—C21—H21A119.1
C2—C7—C8106.95 (13)C16—C21—H21A119.1
C2—C7—C6121.66 (13)O1—C22—H22A109.5
C8—C7—C6131.38 (13)O1—C22—H22B109.5
C9—C8—C13118.97 (14)H22A—C22—H22B109.5
C9—C8—C7134.61 (15)O1—C22—H22C109.5
C13—C8—C7106.42 (13)H22A—C22—H22C109.5
C10—C9—C8119.10 (17)H22B—C22—H22C109.5
C10—C9—H9A120.5O2—C23—H23A109.5
C8—C9—H9A120.5O2—C23—H23B109.5
C9—C10—C11121.15 (17)H23A—C23—H23B109.5
C9—C10—H10A119.4O2—C23—H23C109.5
C11—C10—H10A119.4H23A—C23—H23C109.5
C12—C11—C10121.47 (16)H23B—C23—H23C109.5
C12—C11—H11A119.3O3—C24—H24A109.5
C10—C11—H11A119.3O3—C24—H24B109.5
C11—C12—C13117.78 (16)H24A—C24—H24B109.5
C11—C12—H12A121.1O3—C24—H24C109.5
C13—C12—H12A121.1H24A—C24—H24C109.5
N1—C13—C12130.61 (15)H24B—C24—H24C109.5
N1—C13—C8107.89 (13)
C13—N1—C2—C70.40 (16)C7—C8—C13—N1−1.05 (16)
C13—N1—C2—C3−177.03 (13)C9—C8—C13—C12−2.2 (2)
C14—N4—C3—C2177.49 (12)C7—C8—C13—C12178.47 (13)
C5—N4—C3—C254.04 (14)C3—N4—C14—C15170.60 (11)
C7—C2—C3—N4−16.43 (19)C5—N4—C14—C15−67.03 (15)
N1—C2—C3—N4160.63 (13)N4—C14—C15—C1756.04 (16)
C14—N4—C5—C1639.91 (15)N4—C5—C16—C17−5.02 (19)
C3—N4—C5—C16162.27 (11)C6—C5—C16—C17−127.70 (15)
C14—N4—C5—C6165.02 (11)N4—C5—C16—C21176.81 (12)
C3—N4—C5—C6−72.62 (13)C6—C5—C16—C2154.14 (17)
N4—C5—C6—C747.51 (15)C21—C16—C17—C18−2.5 (2)
C16—C5—C6—C7172.59 (11)C5—C16—C17—C18179.38 (13)
N1—C2—C7—C8−1.06 (17)C21—C16—C17—C15174.74 (13)
C3—C2—C7—C8176.37 (13)C5—C16—C17—C15−3.4 (2)
N1—C2—C7—C6178.11 (13)C14—C15—C17—C16−21.95 (19)
C3—C2—C7—C6−4.5 (2)C14—C15—C17—C18155.21 (13)
C5—C6—C7—C2−11.52 (19)C16—C17—C18—C191.3 (2)
C5—C6—C7—C8167.41 (14)C15—C17—C18—C19−175.89 (14)
C2—C7—C8—C9−177.88 (16)C23—O2—C19—C18−21.5 (2)
C6—C7—C8—C93.1 (3)C23—O2—C19—C20158.32 (15)
C2—C7—C8—C131.28 (16)C17—C18—C19—O2−179.63 (13)
C6—C7—C8—C13−177.76 (14)C17—C18—C19—C200.6 (2)
C13—C8—C9—C101.1 (2)C22—O1—C20—C213.5 (2)
C7—C8—C9—C10−179.79 (16)C22—O1—C20—C19−175.59 (13)
C8—C9—C10—C110.2 (3)O2—C19—C20—O1−1.91 (19)
C9—C10—C11—C12−0.6 (3)C18—C19—C20—O1177.89 (12)
C10—C11—C12—C13−0.4 (2)O2—C19—C20—C21178.95 (12)
C2—N1—C13—C12−179.03 (15)C18—C19—C20—C21−1.3 (2)
C2—N1—C13—C80.44 (16)O1—C20—C21—C16−179.02 (13)
C11—C12—C13—N1−178.76 (15)C19—C20—C21—C160.0 (2)
C11—C12—C13—C81.8 (2)C17—C16—C21—C201.8 (2)
C9—C8—C13—N1178.27 (13)C5—C16—C21—C20−179.92 (13)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1A···O30.907 (19)1.982 (19)2.880 (2)170.1 (16)
O3—H3···N4i0.91 (2)1.95 (2)2.840 (2)165 (2)
Symmetry code: (i) −x, −y+1, −z+1.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1A···O30.907 (19)1.982 (19)2.880 (2)170.1 (16)
O3—H3···N4i0.91 (2)1.95 (2)2.840 (2)165 (2)
Symmetry code: (i) −x, −y+1, −z+1.
 

Acknowledgements

We gratefully acknowledge diffractometer support by the Institute of Bioorganic Chemistry of Uzbek Academy of Sciences, Uzbekistan.

References

First citationOxford Diffraction (2009). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.  Google Scholar
 First citationSaidov, A. Sh., Alimova, M., Levkovich, M. G. & Vinogradova, V. I. (2013). Chem. Nat. Compd. 49, 302–304.  Web of Science CrossRef CAS Google Scholar
 First citationSaidov, A. Sh., Alimova, M. & Vinogradova, V. I. (2014). IJCPS, 3, 9–12.  Google Scholar
 First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
 First citationWestrip, S. P. (2010). J. Appl. Cryst. 43, 920–925.  Web of Science CrossRef CAS IUCr Journals Google Scholar
 First citationYu, H.-T., Vela, M. A., Fronczek, F. R., McLaughlin, M. L. & Barkley, M. D. (1995). J. Am. Chem. Soc. 117, 348–357.  CSD CrossRef CAS Web of Science Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 71| Part 8| August 2015| Pages o574-o575
https://doi.org/10.1107/S2056989015013286
Follow Acta Cryst. E
Sign up for e-alerts
E-alerts
Follow Acta Cryst. on Twitter
Twitter
Follow us on facebook
Facebook
Sign up for RSS feeds
RSS